Paddy Whacked: The Untold Story of the Irish American Gangster

Summary

Here is the shocking true saga of the Irish American mob. In Paddy Whacked, bestselling author and organized crime expert T. J. English brings to life nearly two centuries of Irish American gangsterism, which spawned such unforgettable characters as Mike "King Mike" McDonald, Chicago's subterranean godfather; Big Bill Dwyer, New York's most notorious rumrunner during Prohibition; Mickey Featherstone, troubled Vietnam vet turned Westies gang leader; and James "Whitey" Bulger, the ruthless and untouchable Southie legend. Stretching from the earliest New York and New Orleans street wars through decades of bootlegging scams, union strikes, gang wars, and FBI investigations, Paddy Whacked is a riveting tour de force that restores the Irish American gangster to his rightful preeminent place in our criminal history -- and penetrates to the heart of the American experience.

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Paddy Whacked - T. J. English

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introduction

Who would have guessed that in the early years of the twenty-first century—in an era of rampant jihadism and global paranoia—the highest ranking organized crime figure on the Federal Bureau of Investigation’s (FBI) Ten Most Wanted List was neither a Mafia don nor a Latin American narcotraficante nor a Russian mafiya, but rather an old-style Irish American mob boss from around the way?

During the years of his reign, James Whitey Bulger, formerly the kingpin of South Boston, was like a character out of an old Cagney movie—tough but sentimental, kind to his mother, politically connected, and a ruthless sociopath who murdered at least nineteen people. Bulger created a criminal organization based in Southie that ruled the roost for over twenty years, from the early 1970s until 1995, when Bulger was tipped off that the Feds were coming to get him and went on the lam. The Age of Bulger transpired during a time when most U.S. citizens probably thought the Irish American gangster no longer existed outside of black-and-white Warner Bros. movies from the 1930s. Bulger not only existed, but he also thrived, making millions of dollars annually through racketeering, killing people at will, and getting away with it through expert manipulation of the System. He eluded capture and prosecution in a manner that would have made a Mafia boss like John Gotti weep with envy.

As an Irish American gangster, Bulger flew mostly below the national radar. Certainly in the later decades of what was an unprecedented 150-year run for the Irish Mob, old-style mobsters like Whitey were content to operate in the shadows. Let the mafiosi walk the red carpet, their exploits made larger-than-life by the likes of Brando, DeNiro, and Pacino. Let the Italians come under the scrutiny of the FBI, which during Director J. Edgar Hoover’s administration had denied the existence of the Mafia, but would eventually go after La Cosa Nostra with the zeal of a jilted lover. Each headline-grabbing arrest and prosecution of LCN made it possible for the FBI and other law enforcement agencies to promote their own exploits, creating a self-fulfilling mythology that was great for the G-Men but not so great for the Italians. With the Mafia dominating the headlines, the Irish Mob soldiered on mostly by staying local, keeping their operations small, and working within underworld parameters that had been in place for more than a century.

Whitey Bulger may have been the last of the last, a man whose staying power was unique to South Boston, but the circumstances of his rise in the underworld were the result of a long and violent history. Like most Irish American mobsters, his power was based in part on two major elements: He had a corrupt FBI agent in his pocket and a younger brother in the State House, Massachusetts State Senator William Bulger. The degree to which Whitey was able to finagle these two factors—the lawman and the politician—was part and parcel of his inheritance as an Irish American gangster.

Like a neighborhood godfather from long ago, Bulger doled out turkeys to the needy on Thanksgiving and Christmas, lent money to school kids, did favors for his constituents, and settled local disputes. He understood the aggrieved nature of the Irish in Boston, whose legacy was fundamentally the same as that of the Irish in New York, Chicago, Philadelphia, early New Orleans, and myriads of other U.S. municipalities large and small. The ravages of colonialism, famine, pestilence, anti-Irish and anti-Catholic bigotry had shaped the Irish American identity and created a people who were sometimes criticized for being clannish or overly parochial. The Irish themselves didn’t see it that way. Arriving in America en masse under the most dire circumstances imaginable, they did what they had to do: They looked out for one another and created social systems that allowed them to advance, even though American society at large was determined to keep them in their place.

It is a common misconception among most people—even many Irish Americans—that the American Mob began as an Italian institution transplanted directly from Sicily. Indeed, criminal traditions in Sicily, known variously as vendetta societies or la Mafia, were transported to the United States with the beginnings of Italian immigration in the late 1880s and 1890s. But the Irish had been in the United States for over forty years by then, and the American underworld—which was based on criminal infiltration of the System for social advancement and economic gain—was already firmly entrenched. The earliest progenitors and organizers of this underworld were Irish refugees whose desire to make it in the New World was informed by oppression, starvation, and the threat of total extermination.

To understand the roots of organized crime in the United States, it is necessary to make a leap of the imagination back to the Old Country. In the early nineteenth century, Ireland was a dreary place, a colony of the British Crown where the Irish people lived as virtual slaves on land that had once belonged to their ancestors. They tilled the soil at the behest of their British landlords who controlled the property through laws that made it nearly impossible for tenant farmers to achieve even a semblance of social mobility, and they could be evicted at any time. The names of all streets and towns had been changed from their original Gaelic into English, and the native language was banned by law. This oppressive colonial system was enforced at the end of the lash and the hangman’s noose.

After a history of failed rebellions and squelched political uprisings, what remained of an anticolonial movement in Ireland was to be found among the secret resistance societies, loosely structured organizations that used a strategy of sabotage and violence to disrupt the colonial government, especially in rural areas of the country. The Whiteboys, the Ribbonmen, and the Molly Maguires were comprised of members of the community who circulated openly, but whose membership in the underground resistance movement was a well-guarded secret. These groups represented the earliest inklings of American gangsterism in that they presented themselves as custodians of their communities and were just as likely to prey on their own people as they were to go after Crown forces.

In 1845, the rural resistance societies and all other forms of social interaction—underground or otherwise—were brought to a halt by a tiny agricultural virus known as Phytophthera Infestans. There had been blights before in the country’s potato crop, which both as a product for export and a food source sustained the nation. Normally, the potato was a hardy tuber that always bounced back. This time, however, the virus struck at the root and spread like wildfire, wiping out the entire crops of 1845, 1846, 1847, and so on. Over a period of nearly a decade, the country’s potato crop was decimated; one-third of the island’s population perished from starvation and disease or were forced to flee into permanent exile.

The Great Potato Famine is a vague and distant memory for most Americans, even though an overwhelming majority of the forty million Americans of Irish descent in the United States can trace their ancestry back to what was the most cataclysmic human event of the nineteenth century. Many of the personality characteristics that were lampooned in U.S. newspapers of the era as typically Irish were a result of famine and mass starvation.

The famine wasn’t just a crop failure; it was politically mismanaged genocide. For nearly a century leading up to the disaster, the economy of Ireland had been artificially engineered to produce one product and one product only. Regressive Corn Laws were passed that made it economically impossible for Irish farmers to make a profit off the export of any product other than the potato. When the crop was wiped out, it was a complete and total devastation for Irish culture. Families starved to death in their cottages or begged in the streets and were reduced to subhuman levels of subsistence. An archdeacon who toured the village of Kenmare wrote, On one road…the deaths are three each day. The people are buried without coffins. I daily witness the most terrible spectacles: women, children, and old men crawling out [of their homes] on all fours, perhaps from beside a corpse, to crave a morsel of any kind.

Another witness wrote, The cries of starving hundreds that besiege me from morning until night actually ring in my ears…. I attended myself a poor woman whose infant, dead two days, lay at the foot of the bed, and four others nearly dead in the same bed…. A famished cat got up on the corpse of the poor infant and was about to gnaw it but for my interference. I could tell you such tales of woe without end.

Bodies were piled like refuse on the side of the road. If it wasn’t starvation that got you, it was famine-related disease. The swollen limbs, emaciated countenances, and other hideous forms of disease are innumerable, wrote a medical relief worker. A dreadful disease is breaking out amongst them. I allude to Dysentery with discharge of blood from the bowels. Another ailment, sore mouth, appeared as well, which I think has been produced by the unwholesome food the poor were obliged to use in the early part of the season and which so injured the coat of their stomachs and bowels, that now they are not in a state to bear strong food and the consequence is the living membrane of the intestine is coming away.

These and other medical reports were delivered to Charles Trevelyan, permanent secretary of the Treasury in London and the man who single-handedly controlled most relief expenditures. The British response to reports of mass starvation in their Irish colony just a few miles across the English Channel has been most charitably characterized as a kind of criminal negligence, best personified in the public comments of Charles Trevelyan. Ireland’s great evil, he stated, was not famine but the selfish, perverse, and turbulent character of the people.

British relief efforts were late and insufficient to stem the tide of disease, death, and exile. And so the Irish masses took to the seas, carrying with them a deep-seated bitterness over the genocidal mismanagement of their British overlords, along with a legacy of shame, desperation, and famine-related dementia.

At sea, the Vale of Tears continued, with thousands of refugees dying on the coffin ships, in which disease spread among the multitudes crammed together in steerage. All told, the Great Famine lasted ten years, from 1845 to 1855. In a country of eight million, one million died, and another million and a half were forced into exile hoping to find refuge in places like Liverpool, Australia, Canada, and especially the United States.

The ways in which the Irish were able to establish a foothold in the United States were inexorably linked with the growth and development of the country’s most vibrant cities. What was not eradicated during the famine years was the innate sociability of a people who believed in the power of human interaction. The saloon, the parish hall, and the political clubhouse became the foundation of an immigrant dynasty where the terms of survival and social advancement were negotiated and dispensed according to a person’s willingness to play the game.

In the history books, much has been made of early Irish Americans’ use of Tammany Hall, the vaunted nineteenth and early twentieth century political organization, as a means of consolidating power. The implication is that Tammany politics and all that they represented were an Irish creation, a veritable hijacking and perversion of the democratic process. In truth, Tammany Hall existed from the beginning of the American republic. It was founded in Philadelphia in the years immediately following the American Revolution as a social, fraternal, and benevolent organization. Named after Saint Tammany, a mythical Indian chief rooted in American Indian lore, the organization was designed as a means for exerting influence over the political process. Members elected their leader, known as a grand sachem, and sought to influence legislation favorable to their own business interests.

This system was in place for nearly a century by the time of the Great Potato Famine and the huge Irish influx of the 1840s, 1850s, and 1860s. In New York, where Tammany Hall had by then consolidated most of its power, Irish immigrants worked their way into the Tammany structure like salmon swimming upstream to spawn. They became precinct captains, ward bosses, and aldermen, injecting energy and imagination into an elaborate ward system that dispensed favors and provided an edge in exchange for a vote. Tammany put forth candidates, mostly Democrats, under their banner, and the entire Machine was well-represented by the organization’s official symbol—a ferocious Bengal tiger.

The Tiger became the short-hand name for an organization that was to become the model for like-minded political machines located far beyond the boundaries of New York. In cities large and small, political machines dominated by first and second generation Irish Americans became a common mode of localized government that lasted well into the next century. In many ways, Irish-style politics became the politics of America, especially within the ranks of the Democratic Party, whose benevolent stance toward immigration, the working man, and ethnic politics in general can be traced to the first great influx of Irish immigration.

Organized crime was, in many ways, a natural outgrowth of the Tammany structure. Director Martin Scorcese’s movie Gangs of New York (2002), based on a venerable 1927 book by Herbert Asbury, is somewhat misleading when it determines that the beginnings of organized crime occurred within the universe of the early Irish gangs. In fact, the gangs operated at the behest of the political apparatus. They were the muscle that lurked behind the symbol of the Tammany Tiger, their unique skills most notably required on election day when all political parties—Democratic, Whig, Republican, and Native American—unleashed their bully boys to police the polling sites.

The vast universe of criminal rackets that flowed from the daily workings of the Machine became the basis for organized crime in the United States. Municipal corruption, graft, boodling, illegal gambling and prostitution proceeds, street-level extortion, and gangsterism were a consequence of men and women maneuvering for power, clawing and scratching to gain a foothold within the Machine structure and advance in society.

Despite wars, sporadic corruption scandals, changing political administrations, and the exigencies of the American economy, this remained the model for organized crime in the United States until the years of Prohibition, which changed everything. Prohibition provided something the underworld never had before—a single, dominating racket that was so profitable that it tipped the balance of power. With the establishment of illegal booze as an unprecedented source of profit and influence, the gangsters were now calling the shots, not the politicians.

For Irish American mobsters and their fellow travelers, Prohibition represented the glory years, a time of social ascendancy and high profits in which the gangster became a kind of cultural archetype. New York and Chicago evolved into the central domains of a vast, interconnected underworld that included not only mobsters and bootleggers, but also politicians, judges, lawyers, ward bosses, speakeasy operators, financiers, corporate overseers, police precinct captains, cops on the beat, and corrupt federal agents who made it all possible. In many ways, the era was the culmination of a way of doing business that had begun seventy years earlier with the first wave of desperate, destitute refugees from Paddy’s green shamrock shores.

Things began to change with the end of Prohibition in 1933, and the Irish Mob took an even greater hit during the years of the New Deal. A number of prominent practitioner’s of Machine politics were prosecuted or forced from office via corruption scandals. Political reforms were enacted that brought about an end to the long era of the Machine.

In the years following World War II, the Irish American gangster scattered far and wide. Many were absorbed into the labor movement, either as strikebreakers hired by corporations, or as tough guys and facilitators connected with trade unions, most notably the International Longshoremen’s Association (ILA) and the International Brotherhood of Teamsters. Some Irish American gangsters became notorious hitmen for hire who carried out murder contracts either for forces in the labor movement or for the Mob, also known as the Syndicate or the Outfit, which was a consortium of multiethnic mobsters. The Italian Mafia—a faction within the Mob that gained such a grandiose level of cultural notoriety in the later decades of the twentieth century that it came to represent the Mob itself—frequently employed Irish gunmen, particularly if the intended target of a hit was an Irishman.

The image of the independent Irish American criminal, a man who went wherever the money was, became a common trope in the underworld of the 1960s, 1970s, and 1980s. Working-class hoods who usually specialized in a specific brand of criminal activity—whether it was B & Es (breaking and entering), safe cracking, the snatch racket (kidnapping), murder-for-hire, or body disposal—saw themselves as underworld tradesmen. (One Irish American hitman of this era even referred to what he did as carpentry work.) Often, these were men who wound up on the losing end of a long, ongoing rivalry between Irish and Italian mobsters that was rooted deep in the history of the American underworld. With a far larger and more organized structure, Italian organized crime groups inevitably dominated these confrontations, leaving a trail of dead Irishmen across the land.

Far more successful for the Irish were the neighborhood-based gangs that came to represent the last of the Irish Mob. In New York and Boston, the Irish Mob remained a viable force in the underworld long after most Irish Americans had assimilated into the suburbs and became generic white people in America. Mobsters in these cities inherited certain criminal rackets that had traditionally been controlled by Irish gang factions going back more than a century. The Westies gang in New York and Whitey Bulger’s Winter Hill Gang in Boston were comprised of tough-talking, street-savvy Irish hoods who appeared to be caught in a time warp. They were tough, emotional, paranoid men who adhered to the underworld dictum that three men can keep a secret, but only if two of them are dead.

The fact that the Irish Mob in its later decades engaged in a kind of macabre, internalized violence that can only be characterized as self-destructive should not be surprising. When a vast, morally corrupt universe that has murder as its ultimate principle goes through a kind of death throes, violent thrashing and internal self-immolation are the likely result. The Irish American gangster was always known for his wild, impulsive, antisocial behavior, which certainly characterized the last bloody days of the Irish Mob in America.

The main events of this saga take place in New York, Chicago, and Boston, with side trips to New Orleans, Kansas City, and Cleveland. Although the Irish Mob did not have the kind of initiation rights or agreed-upon rules of interaction that made Cosa Nostra such a cohesive underworld force throughout the United States, there were certain social systems put in place by the Irish that were remarkably similar in all of the aforementioned municipalities. An Irish mobster in Chicago might not be bound by the same rules as an Irish mobster in Boston, but the way they went about conducting business in these different cities made it seem as if Irish underworld players had all gone to the same divinity school. Whereas the Mafia was a private club, the Irish Mob was more of a philosophy, a shared social contract characterized by a loosely-connected sphere of influence in which the underworld and upperworld intersected under the guise of the lawman, the politician, and the gangster.

The men and women who populate this long march through the underbelly of American society are not easy to characterize. At the street level, there are numerous examples of the kind of doomed, untamed desperado who would come to symbolize the Irish gangster for many Americans. Leaders and followers populate this yarn, as do sociopaths and tragic cases. Many of their lives were tawdry, some downright despicable, but they were almost never boring. The life of the gangster was harsh, dangerous, fraught with paranoia, and sometimes exciting to the point of delirium.

The history of the Irish Mob includes a fair number of criminal visionaries, men and women who might have done well for themselves if they had applied their skills to more legally acceptable modes of commerce. The Irish Mob stretched into the legitimate world, more than most underworld fraternities, entangling the fortunes of untold policemen, federal agents, union men, political figures, and at least one prominent tycoon whose lifelong dalliance with the underworld changed the course of U.S. history.

Over the decades, much hot air and ink has been expended in the media’s attempt to understand why the rise and fall of the gangster has remained such an enduring myth throughout the country’s history. Certainly part of the attraction is the way in which the underworld has become a metaphor for American capitalism. Anyone who has tried to get ahead and make a living in the United States, from the lowliest street vendor to the most powerful corporate CEO, recognizes the brutal, dog-eat-dog reality of the American Dream. Some fantasize about taking matters into their own hands. In defiance of the laws and mores of polite society, the gangster does just that. In fact, everything about the gangster’s life is a rebuke to the mundane, everyday life of the solid citizen. He lives in the moment, pursues immediate gratification with reckless abandon, and revels in his own narcissism like a slop-house pig. The gangster lives according to his own rules, as if he were judge, jury, and executioner—as if he were God.

There must be a little something of the suppressed gangster in the imagination of many people, given the prominence of gangster lore in popular culture. This tradition far precedes the most recent cinematic incarnations. From the days of the earliest newspapers and photographs to the present, Americans have exhibited a fascination and identification with the dark recesses of American commerce.

The American mobster as we perceive him today—violent, impulsive, disreputable, often irredeemable—is tethered to the earliest days of the Irish immigrant experience, when the Mob was born out of starvation, disease, desperation, and bigotry. Over the last century and a half, men and women of innumerable ethnicities and social backgrounds have taken a bite of the apple, from the lowliest criminal to the most esteemed members of society. But for sheer audacity and reckless ambition, few plied their trade with as much staying power or as much panache as the originator: the Irish American gangster.

PART One

birth of the underworld

CHAPTER # One

1. blood at the root

John Morrissey was a young ruffian—a teenage, Irish punk with no job, no money, and few possessions other than the clothes on his back. The year was 1849, and Morrissey had just arrived in New York City from the upstate town of Troy, where he had been raised after moving from Ireland with his parents at the age of three. In Troy, Morrissey developed a reputation as a brawler and a troublemaker. He’d been indicted for burglary, assault, and assault with intent to kill; served a sixty-day stint in the county jail; and was under constant harassment from local authorities. They said eighteen-year-old Morrissey was a gangster, but the young man knew in his heart that his ambitions were too great for that two-horse town. And so, possessing a restless energy that could not be contained in the placid, confined roads of small-town America, he set out for the great metropolis 160 miles to the south, where pilgrims, immigrants, and refugees were presently arriving in droves.

Morrissey knew exactly where he needed to go: the Empire Club, a gambling parlor and political clubhouse that was famous throughout the state. Located on Park Row in lower Manhattan, the club was the home base of Captain Isaiah Rynders, legendary sporting man, gambling impresario, and political fixer for the Democratic party. Rynders was the employer of hundreds of political operatives, gambling club workers, saloon keepers, and gangsters; his organization was at the heart of a political machine that made the great city hum. Morrissey—hungry, hard-headed, and propelled by the desires of youth—was determined to harness the power of Rynders’s organization to raise himself out of the ghetto and make his mark in the world.

He arrived at the Empire Club on one June afternoon, stood overlooking the gaming tables and declared, I’m here to say I can lick any man in this place.

Captain Rynders himself, presiding at a gaming table, looked up at the intrepid young man—five-foot-eleven inches tall, maybe 175 pounds, with a barrel chest and hands the size of meat hooks; impressive, yes, but not so imposing that he could intimidate with sheer physical presence alone.

And who might you be? Rynders asked the young Irishman.

My name is John Morrissey, and I’m the toughest pugilist on the eastern seaboard. I’m here to prove it.

Rynders pursed his lips in an enigmatic Mona Lisa-smile for which he was famous and glanced around at his fellow club members. He assessed the brash youngster, looking him over from head to toe, then nodded for his underlings to advance. They descended upon the young punk with fists, bottles, chairs, slung shots, and other weapons. Morrissey more than held his own until Big Tom Burns smacked him behind the ear with a spittoon, knocking the young hooligan unconscious.

When Morrissey awoke he was laying on a cot in the back of the Empire Club with a knot the size of an acorn on the crown of his skull. Captain Rynders, dressed in finery the likes of which Morrissey had never seen before, stood over the bruiser and said, You’re a bold, young bastard.

Morrissey felt the lump on his head and said nothing.

I want you to come work for me. You’ll make a fine shoulder-hitter for the organization. You can stay at my boarding house and work the docks.

And so began the political career of young John Morrissey.

He was put to work as an immigrant runner, one of hundreds who worked Castle Garden wharf in lower Manhattan, where the immigrant ships disgorged their human cargo. Each day he watched the arrival of his countrymen, and his heart ached at what he saw.

Having been born in Templemore, County Tipperary in 1831 and raised in an Irish slum in America, Morrissey knew a thing or two about poverty. In Troy, whenever his father was able to find work, it had been at the local wallpaper factory or on the docks alongside other Irish laborers. Young John had grown up believing his family was dirt poor, but what he saw at Castle Garden made him reassess his circumstances. Gaunt, haunted Irish peasants arrived by the boatload, weak from dropsy and gout, clinging to satchels that contained all that they owned. They told shocking tales of the Great Famine that had ravaged the Old Country over the last few years and of the horrific, disease-ridden journey across the ocean in hopes of a better future.

It was Morrissey’s job to greet these new arrivals and direct them to soup kitchens and boarding houses controlled by the Rynders organization. Mixed in among the many legitimate immigrant runners were dozens of con artists and land sharks, men who preyed upon the ignorant new arrivals. Later accounts of the era often characterized the job of the immigrant runner as that of a parasite, which may have been a bit harsh. Certainly the position straddled the line between charity and exploitation. Among runners, Morrissey developed a reputation as a tough though fair man who directed hundreds of desperate immigrants to food and lodging. In exchange, they signed voter cards and pledged their support to the political organization that Morrissey represented. On election day, it was Morrissey’s job to see that these people delivered on their pledge—under the threat of violence, if necessary.

Along with tens of thousands of other Irish immigrants arriving in New York City on a monthly basis, Morrissey found lodging in Five Points, the infamous slum neighborhood that dominated the Sixth Ward at the lower tip of Manhattan island. For a time, he lived in a boarding house on Cherry Street and frequented a grog shop, or speakeasy, on lower Broadway known as the Gem Saloon.

Five Points was a lively area though the physical conditions of the district were awful. Laid out on top of what had once been a sewage pond known as the Collect, Five Points had evolved from being mostly an industrial district of tanneries, glue factories, and turpentine distilleries to a residential haven for the city’s growing immigrant class. Poor Germans, Irish, Jews, and African Americans were crowded into two-story wooden structures built unsteadily on landfill over Collect Pond.

The district contained what was ostensibly the nation’s first tenant house, or tenement. The Old Brewery was a former beer factory that had been converted into living quarters. A five-story monstrosity that glowered over the Five Points district like a slovenly toad, the building housed an impoverished collection of newly arrived immigrants and freed African Americans. For less than two dollars a month, lodgers resided in conditions that were stifling, overcrowded, and with a sanitation system so haphazard that the building and surrounding area were sometimes buffeted by waves of cholera that reached epidemic proportions.¹

Fetid conditions in the Old Brewery almost guaranteed that the building would become the center of much violence and depravity in the district. In the sprawling basement, known locally as the Den of Thieves, gambling, organized dog fights, prostitution, and all manner of robbery and assault were not uncommon. For local authorities, be they police or officials of the Association for Improving the Conditions of the Poor (AICP), the Old Brewery was a virtual no-go zone; the belief was that if you entered uninvited you were not likely to come out alive. Within the building’s many warrens and hallways, violent crimes—including rape and murder—were so commonplace that years later, when the building was finally demolished, observers claimed to see construction workers carrying out bags of bones belonging to numerous murder victims who had been buried beneath the building’s floorboards and in the walls.

The abysmal conditions in the Old Brewery spilled out into the district, creating an area that became well-known for general licentiousness and depravity. There was a saloon or speakeasy on nearly every corner with drunks stumbling out into the streets to be jack-rolled by gangs of prepubescent hooligans. Organized thievery was also common, with a high concentration of pickpockets, sneak thieves, and con artists of every variety. At night, the district descended into a kind of hellish debauchery; practically every other tenement was set up as a house of assignation, and basements and backrooms were designed for even more adventurous commercial sex practices. Gaming and backroom dance parlors were also common and eventually gave rise to a vibrant new dance style that was a combination of the African American shuffle and the Irish jig. This style was called a break down and became the forerunner of modern tap dancing.

By the time of John Morrissey’s arrival in Five Points, the dangerous and licentious nature of the area had become something of a drawing card. Numerous writers and social commentators had recently visited the area to gawk at and pass judgement upon its inhabitants. In 1841, Charles Dickens, the great social observer and illustrious English novelist, immortalized the neighborhood in American Notes, an account of his five-month tour of North America:

Let us go again…and plunge into Five Points. Poverty, wretchedness, and vice are rife enough where we are going now…. This is the place, these narrow ways diverging to the right and left, and reeking everywhere with dirt and filth…. Debauchery has made the very houses prematurely old. See how the rotten beams are tumbling down, and how the patched and broken windows seem to scowl dimly, like eyes that have been hurt in drunken frays…. Vapors issue forth that blind and suffocate. From every corner, as you glance about you in these dark streets, some figure crawls half-awakened, as if judgement hour were near at hand…. Here, too, are lanes and alleys paved with mud knee deep; underground chambers where they dance and game; ruined houses open to the street, whence through wide gaps in the walls other ruins loom upon the eye, as though the world of vice and misery had nothing else to show; hideous tenements which take their names from robbery and murder; all that is loathsome, drooping, and decayed is here.

But of all the conditions that made Five Points legendary, the physical environment was but a garland compared to its reputation as the world’s preeminent stomping ground for gangs and gangsters. John Morrissey was well-acquainted with the life of the gangster. Back in Troy by the age of sixteen, he had become leader of the Downtowns, a small gang of mostly Irish and German teenage hooligans who often battled with the Uptowns, an anti-immigrant gang of American-born youths. The Uptowns frequently raided their territory in the riverfront industrial area of town. It was as leader of the Downtowns that Morrissey acquired his criminal record and also his reputation as a skilled street fighter who was adept with his fists.

In Five Points, fists were a throwback to a more innocent time. Even the Irish shillelagh, the oaken cudgel that had been a part of Celtic battles since the ancient days of clan warfare, was obsolete in Five Points, where hatchets, knives, slung shots, spiked clubs, brass knuckles, tomahawks, and muskets were among the more common implements of confrontation.

The gangs were ubiquitous and tended to strut their stuff in two main areas. The primary gathering place was Paradise Square, where Canal Street, the Bowery, Chatham, Pearl, and Centre Streets converged to form a truncated triangle, giving the neighborhood its name Five Points. Paradise Square was claimed by the earliest of the gangs, mostly Irish, including the Forty Thieves, Kerryonions, Shirt Tails, Chichesters, Patsy Conroys, Plug Uglies, Roach Guard, and Dead Rabbits. The other staging area for the gangs was the Bowery, which extended north of Five Points. Here were established the social clubs and headquarters of the native-born American gangs, most notably the Bowery Boys, the True Blue Americans, and the American Guard.

The gangs were a highly visible presence in Five Points, particularly during daylight hours, when they traveled brazenly in packs. By 1850, when John Morrissey was living on Cherry Street, the gangs had begun to claim various streets and territories as their own. Some of the gangs identified themselves with special colors or clothes. The Plug Uglies wore hi-top derbies stuffed with padding so they could use their noggins as battering rams; the Shirt Tails wore their shirts untucked; the Dead Rabbits sewed distinctive, red stripes down the outer seam of their pants to distinguish themselves from the Roach Guard, who wore blue stripes.

For the newly arrived Irish, coming from a land where colonial oppression had been the rule of law for generations, the formation of a gang carried with it the whiff of a noble gesture. These loosely organized street-corner crews were not primarily criminal organizations—not yet, anyway. Many were local versions of regional protection groups, or political resistance sects from the Old Country. Back on the Emerald Isle, these secret, loosely-structured organizations waged guerilla warfare against the British Crown’s commercial and military occupation. In America, what remained were the names, which became bastardized English-language versions of the original Gaelic. Plug Uglies, for instance, was an English translation of baill oglaigh, which meant member of the volunteers. Patsy Conroys was an anglicization of páirt sa chonradh (partners in league). The Whyos, a gang based in Five Points that became prominent later in the century, derived their name from the Gaelic uathadh uais (noble few).²

A gang was comprised of anywhere between ten and one hundred members. The largest of the gangs were the Dead Rabbits, who were a conglomeration of numerous Paradise Square gangs that came together under one banner. It was said that the gang’s name derived from the fact that they carried a dead rabbit impaled on a stick as a calling card. More likely, the gang’s name came from the Gaelic "dead ráibéad. In the vernacular of the times, dead was an intensifier that meant very." Ráibéad, in Gaelic, was a galoot or big lug. Thus, a Dead Rabbit was a very big galoot. The Dead Rabbits had no leader, as such; they were broken down into subdivisions and spread throughout the Five Points district.

With so many hungry, idle young men gathered in green grocery speakeasies and on street corners, confrontations between groups were inevitable. The fights were sometimes barroom donnybrooks that spilled out into the streets, or more serious riots that grew out of organized social and political agitation. By far the most famous gang battles were those between the Dead Rabbits and Bowery Boys, but there were also smaller fights between factions of the Forty Thieves, Plug Uglies, and True Blue Americans. Some of these riots were territorial in nature—Irish versus Irish—but most were racial—native-born Americans versus the nigger Irish.

As recounted in the New York Herald, the Police Gazette, Frank Leslie’s Illustrated News, and other periodicals of the day, the gang wars could be shockingly brutal. In rural Ireland, some of the immigrants had belonged to fighting clubs in which altercations were fought according to Shillelagh Laws, where the primary instrument of battle was the Irish stick. In America, there were no rules. Sometimes gang riots raged sporadically for two or three days, with the streets barricaded by barrels and carts while gangsters blazed away with muskets and pistols, or tussled up close with brickbats, bludgeons, fists, and teeth. Most of the combatants were men, but women also played a role, either as lookouts or as resuppliers of ammunition. A few women even achieved renown as fierce battlers, none more so than Hellcat Maggie, who fought alongside the Dead Rabbits in many of their battles with the Bowery Boys and other nativist gangs. A young woman no more than twenty-years-old, Hellcat Maggie is reported to have filed her teeth sharp as mini-daggers and wearing on her fingers long, artificial nails made of metal. She would descend on rival gang members like a screaming banshee, biting and clawing until her fingers were dripping with the blood of her enemies.³

With casualty totals numbering in the hundreds and a level of carnage and destruction that frequently necessitated calling in the National Guard, the gang wars were a disturbing byproduct of the times. The gangs were a potential powder keg. Sprawling and disorganized, comprised mostly of rural Irish peasants now living in a strange and terrifying new environment, they haunted the streets of Five Points like spectral figures from some pre-utopian version of the American Dream. Mostly leaderless, the gangs were replenished weekly by the waves of destitute famine refugees arriving at Castle Garden wharf and other immigrant ports-of-call. The bitterness and sense of displacement that characterized the immigrant rabble was a potent force just waiting to be organized and harnessed. Anyone who could find a way to focus the frightening energy of the gangs, to tame the wild beast and redirect its power toward some useful purpose, would be a formidable leader indeed.

Old Smoke Riseth

By mid-1851, John Morrissey had established himself as a young man on the move. Through his activities as an immigrant runner and as a political organizer for Captain Isaiah Rynders’s Empire Club, he had cobbled together a small financial nest egg that made it possible for him to buy in as part-owner of the Gem Saloon. Being a saloonkeeper was an essential first step for anyone hoping to launch a career in politics. Morrissey’s ambitions were somewhat hindered by the fact that he could neither read nor write, a fact he sought to rectify through long hours of tutoring and study in the back of his saloon.

The young Irishman also had aspirations as a professional boxer, which, in the rough-and-tumble world of nineteenth century America, would be instrumental to a career in politics. Men hoping to achieve elective office needed to have a following; the saloon and the boxing ring were two arenas in which a man could distinguish himself as both tough and popular. Young John Morrissey was no exception. He launched his boxing efforts in the Five Points, where he had earned the catchy sobriquet of Old Smoke.

He’d first been given the nickname at an indoor shooting gallery in the basement of the St. Charles Hotel. One evening Morrissey became engaged in an impromptu fistfight with a man named Tom McCann, an American-born hoodlum affiliated with the Bowery Boys gang. The numerous onlookers who wagered on this fight were especially amazed when McCann pinned Morrissey against a stove of burning coals. Morrissey’s clothes sizzled and smoked, and the smell of burning flesh filled the room, but the Irishman never uttered a word of complaint. In fact, he eventually broke free from McCann’s grasp and whipped his competitor into submission. From then on, Morrissey was respectfully referred to as Old Smoke, a fighter who was able to endure pain and even gain strength and resolve through adversity.

In early 1852 Morrissey officially began his career as a professional pugilist, even though the sport was illegal at the time. Bouts were usually held at secret locations, often on piers and barges to avoid raids by coppers. The fights themselves were bare-knuckled affairs fought according to London Prize Ring rules, which meant each round continued until one of the fighters was knocked off his feet. There was no set limit to how long a fight could last; the bout continued until one of the fighters either quit or could not answer the bell for a new round. Competitive boxing matches were brutal, bloody, and known to last as long as sixty or seventy rounds, sometimes with deadly results.

For his first major championship bout, Morrissey traveled all the way to California. At Mare Island in San Francisco Bay, Old Smoke fought and defeated the California state champion, George Thompson, in nineteen minutes for a purse of $4,000 and a side bet of $1,000. It was in San Francisco that Morrissey also made his debut as a gambling impresario, running a popular dockside faro game from which he amassed a sizable bank roll. One night, a local man named Jim Hughes claimed that he had been cheated.

I challenge you to a duel, Hughes said to Morrissey, so that I may restore my lost honor.

So be it, replied Morrissey. May I choose the weapons?

Of course, said Hughes.

The following night a crowd gathered in expectation of the agreed upon showdown, which never took place, for Jim Hughes fled in terror when Old Smoke Morrissey appeared on the field of honor with a pair of butcher’s cleavers under his arms.

The New York Irishman returned home more popular than ever. He fought again in October 1853, this time against the man who was the recognized champion of the world, Yankee Sullivan, an Irishman by way of Australia whose real name was James Ambrose. The fight was held at Boston Corners, a remote, rural location on the border of New York and Massachusetts. An estimated three to five thousand fight fans arrived at Boston Corners that day. They came by train, stagecoach, horse, and foot, all converging on the little hamlet to witness what they hoped would be the fight of the century.

Yankee Sullivan was a skilled champion, but he was forty years old. Morrissey was twenty-two. The younger fighter was highly favored, which is why it came as a shock to onlookers when Yankee Sullivan began pounding Morrissey in the early rounds. Sullivan was a wily veteran; he would unleash a flurry of jabs and hooks on his opponent, and then, when the opponent countered, drop to the ground, taking advantage of the London Prize Ring rules in which a drop ended the round.

According to one account, as the rounds progressed, Sullivan, cool and calculating, went at his man determinedly, pecking, slashing, hammering, connecting three times to one. Morrissey kept on coming, but soon exhibited the most revolting appearance imaginable…his eye was dreadfully swollen, and the blood was flowing in a perfect stream from each nostril. In the thirty-fourth round, Morrissey took a dozen blows without return. The odds, which were posted after each round, quickly changed from the original two-to-one for Morrissey to two-to-one in favor of Sullivan.

By round thirty-seven, the old fox seemed to be in complete command. Morrissey was fading rapidly…his knees shook, and his hands were down and his mind bewildered. But the youngster was amazingly game. After receiving a flurry of blows from Sullivan, he advanced with what looked like the last of his energy. He boxed Sullivan into a corner, wrapped him against the ropes, and began choking him with a forearm—which was perfectly legal according to London Prize Ring rules. A Sullivan partisan, fearing that his fighter was about to lose or be choked to death, jumped into the ring and knocked Morrissey down. This, according to any rules, was a foul. Sullivan then unloaded a roundhouse right on Morrissey, who was still on his knees. Foul number two. All hell broke loose, with various fans rushing into the ring. By the time order was restored, the referee and fight officials declared that Old Smoke Morrissey was the winner and new Champion of America.

John Morrissey returned to Five Points as the people’s champion. He married Sarah Smith, the daughter of a steamboat captain, and suffered one of his few early set-backs in life when his only child died at birth. His wife, Sarah, was a well-bred Protestant; she begged her husband to forego the crude and violent world of boxing. In a letter to the New York Tribune, Morrissey, the self-taught writer and nearly life-long pugilist, announced that he was retiring from the ring, having reached his decision out of an honest desire more becomingly to discharge my duties to my family and society and that my duties to my family and myself require me to devote my time and efforts to purposes more laudable and advantages.⁴

Morrissey may have retired from the ring, but he still carried with him the reputation of being the toughest of the tough. His stature grew accordingly. He invested his boxing proceeds in a number of gambling establishments, one of which, a faro and roulette parlor located at No. 8 Barclay Street, became especially popular among politicians and sporting men. A more downscale gambling den owned by Morrissey was located near Paradise Square and was frequented by members of the Dead Rabbits. Increasingly, Morrissey’s circle of friends spanned two worlds: rich and poor, street hoodlums and connected politicians. Inevitably, some of Morrissey’s followers began to encourage Old Smoke to challenge Captain Isaiah Rynders as the de facto mob boss of Five Points, the man who served as a nexus between the sporting men, the gangsters, and politicians who utilized the Dead Rabbits and other gang members to stuff ballot boxes and intimidate rival voters on election day.

I owe Ike Rynders my career, Morrissey told his friends. He put me to work when I knew not a soul in this town. Morrissey proclaimed that he would not go up against Captain Rynders unless events in the street dictated that he do so—which is exactly what came to pass.

The trajectory of Old Smoke’s life changed forever on the night of July 26, 1854, when he came face to face with William Poole, a notorious nativist shoulder hitter and former Bowery Boy who presided over his own Poole Association. Poole was a butcher by trade, skilled with knives and not bad with his fists either. As a member of the Bowery Boys, he’d been in a number of gang wars with the Dead Rabbits and the Roach Guard. He was a bit of a dandy who wore a long frock coat, slicked his black hair down in an early-vintage pompadour, and tried to pass himself off as an aristocrat. Over six-feet tall and strong as a bull, he was known as Bill the Butcher to friend and foe alike. In recent months, he’d emerged as a popular representative of the Know-Nothing Party, a political organization that was the bane of Irish Catholics throughout the United States.⁵

The Know-Nothing movement began in Pennsylvania and spread to New York, Boston, and as far south as New Orleans; it started out as a secret, anti-immigrant underground that engaged in late-night burnings of Catholic churches, the murder of immigrant leaders, and all manner of organized election-day skullduggery. The criminal nature of the organization’s activities necessitated its secrecy; whenever a member of the gang was asked about the private club, he responded, I know nothing, which is how the movement got its name.

In the wake of the Irish potato famine, which first hit the Emerald Isle in 1845 and continued over the next five to ten years, the Know-Nothing movement rode a wave of racist, jingoistic anti-Irish sentiment that had roots early in the century. In the United States, No Irish Need Apply was a sentiment expressed by American-born employers as far back as the 1830s. Resistance to the Irish was partly religion-based. The United States was a Protestant country. The Roman Catholic Church was viewed not only as a pagan cult with strange customs, but as a foreign-based power with designs on subverting and maybe even overtaking the U.S. system of government. The Catholic church is the handmaiden of the devil, was how Cotton Mather put it when American cities were first being constituted. Through the Know-Nothing movement, Mather’s beliefs became a virulent sub-theme of American society.

Religious intolerance was one thing, but White Anglo-Saxon Protestant (WASP) resistance to any and all immigrants was also an economic imperative with roots in the marketplace. The Founding Fathers had never envisioned a country overrun by starving, illiterate, disease-ridden foreigners. The Irish, in particular, were seen as ignorant, hopelessly anti-authoritarian, clannish, overly emotional, and decidedly un-WASP-like in their strong identification with the common man. The term Mulhoolyism became a popular synonym for what was perceived to be rowdy, primitive behavior. In newspaper editorial cartoons in Philadelphia, Boston, Baltimore, and New York, the Irish were routinely depicted as vaguely simian creatures. One famous cartoonist, Thomas Nast, even established a thriving mini-career lampooning Paddy, whose pug-nosed, slovenly representation was often placed alongside Sambo, the ignorant rural black. Paddy and Sambo became dueling caricatures that personified the white man’s burden within America’s budding Anglo-Saxon republic.

By the time Bill Poole had begun to distinguish himself as a gangster, the Know-Nothings were the shock troops of an American purification movement. Among other things, the official Know-Nothing charter listed their principles as anti-Romanism, anti-Bedinism, anti-Papistalism, anti-Nunneryism, anti-Winking Virginiaism, and anti-Jesuitism. Around 1850, the Know-Nothings split from the Whig Party and became bullyboys for the new American Republican Party, who believed, among other things, that the naturalization period for immigrants should be increased to twenty-one years.

For some time, Bill the Butcher Poole and John Old Smoke Morrissey had been walking opposite sides of the fence. They were, in many ways, mirror images of each other, with Poole as the hero of the Protestant ascendancy and Morrissey a living embodiment of Paddy’s ability to rise above difficult circumstances. The men undoubtedly had crossed paths before, either at political rallies or in the district’s many saloons (Poole’s butcher shop was located in nearby Washington Market). Their bitter rivalry—based on politics, racial animosity, and bragging rights over who was cock-o’-the-walk in the Bloody Sixth Ward—finally came to a head on the night of July 26, 1854 when Morrissey found Poole drinking at the bar of the City Hotel at Broadway and Howard Street.

I hear you’re a wizard with a butcher’s blade, said Morrissey to Poole, but I’d wager you’re a coward at the manly art of fisticuffs.

That sounds like a challenge, Morrissey.

It is indeed, replied Old Smoke.

The two men agreed to meet the following morning at the Amos Street dock (now Christopher Street) to have it out once and for all.

At 7 A.M. the next morning, the two bruisers and their followers arrived en masse for the confrontation. The spectators formed a circle, which served as the ring. As later described in the Police Gazette, the encounter was a donnybrook of legendary proportions:

The fight began with some light sparring, Poole holding himself principally on the defensive as his opponent circled for a chance to close. For about five minutes this child’s play of the giants lasted. Then Morrissey made a rush. But Poole was too quick for him. As Old Smoke made his lunge, Bill the Butcher ducked with remarkable agility and seized him by the ankles. In a flash Poole threw his opponent clean over his head and as Old Smoke went sprawling he had only time to roll over when Poole pounced on him like a tiger. Then followed terrible minutes of fighting…. There was a long gash in Poole’s cheeks where the flesh had been torn by his opponent’s teeth. The blood was streaming from Morrissey’s both eyes…. Not a hand was raised to interfere or favor either contestant during the two or three minutes this inhuman struggle lasted.

The fight ended in what some would call a draw; others claimed that Poole got the best of it. Either way, it did not settle the ongoing rivalry between the Poole and Morrissey factions. Their war continued for months, with numerous tit for tat encounters, until the night of February 25, 1855. In this face-to-face encounter between Morrissey and Poole, two of Morrissey’s henchmen gunned down the infamous Bill the Butcher at Stanwix Hall, a saloon on Broadway. Though mortally wounded, Poole lingered on for fourteen days before delivering his immortal final words: Goodbye boys. I die a true American.

John Morrissey, along with Paudeen McLaughlin, Lew Baker, Jim Turner, and a few minor accessories, was put on trial for the murder. The case resulted in a series of hung juries before charges were dropped altogether, sealing Morrissey’s legend as the man who brought about the demise of Bill the Butcher, one of the great xenophobe’s of American history. Old Smoke Morrissey had been a gangster, a saloon keeper, a boxer, and gambling impresario—now he was an acquitted murderer and the most popular man in the Irish American underworld.

The First Irish Mob Boss

The term mob boss originated in Five Points and refers to a form of spontaneous political activity known as a mob primary. Mob primaries comprised the most basic form of political organization known to man. They were initiated by an aspiring political leader merely standing on a milk crate or soap box and orating until he had gathered a crowd, or mob, who was willing to sign a petition on the man’s behalf declaring him a candidate for public office. The mob pledged its vote to the orator, who was usually a saloon keeper willing to offer free drink, a sandwich, a cellar mattress to sleep on, or all of the above in exchange for a vote. The type of voter most willing to enter into this arrangement was usually a rough character—a bum, a homeless person, a thief, or a gangster. Thus, the mob boss, or mobster, became the leader of a less than savory constituency that was, nonetheless, a powerful force capable of swinging many local elections.

The arrangement worked both ways. By aligning himself with a rising and powerful mob boss, the street hoodlum was now also a mobster. He was connected, part of a system in which he now had a vested interest. Ostensibly, he would now have the kind of protection that was necessary for him to operate an illegal business—say, a house of prostitution, gambling den, burglary ring, unlicensed speakeasy, or any manner of criminal enterprise popular throughout the underworld. A vast subterranean universe of vice, exploitation, and good times, the underworld was kept alive through a steady flow of cash from above and below. From the earliest mob primary in America, the underworld and the upperworld were intrinsically intertwined and would remain so through centuries of bloodshed, criminal prosecution, and political reform.

Since the early 1840s, the most powerful mob boss in New York City was Captain Isaiah Rynders. Rynders was the first to establish a network of saloons and gambling parlors that generated money and created an underworld constituency, which buttressed his political organization, the Empire Club. In 1844 Rynders achieved national fame for himself when he virtually delivered the presidency to James K. Polk, the Democratic candidate. He did so through a highly physical form of voter fraud. The use of gangsters on election day was a common practice of all the political parties, but Rynders was the first to perfect the art by organizing the hoodlums into cohesive voting blocks. In New York, his ability to deliver became the foundation of the powerful political organization, or machine, known as Tammany Hall. Rynders’s record of success was such that he made electoral forays to Philadelphia, Baltimore, and, in 1854, the city of New Orleans, where he sought to educate local Democrats in the ways of Tammany-style machine politics.

Rynders’s only problem was that he wasn’t Irish, at least not Irish Catholic with roots in the Old Country. Although his mother was of Irish Protestant stock, his father was German American. Increasingly, the waves of Catholic famine immigrants who had begun to fill out the ranks of the underworld—and the lower political ranks of organizations like Tammany Hall—clamored for one of their own as titular leader of the Mob. In an era when social mechanisms for change were woefully unresponsive to the needs of the people, the Mob inevitably sought to bring about change in their own way—in the streets. It happened, oddly enough, on Independence Day, 1857.

During that time, the city’s gang wars had grown considerably worse largely due to the fact that New York was patrolled by two competing police forces: The Municipals, who were loyal to the Democratic Party, and the Metropolitans, stepchild of the Republicans. These two forces seemed more interested in fighting each other than actually policing the city (a situation that would be rectified two years later when the two forces were finally combined). The gangsters ran wild during what was an especially dark and turbulent year that would culminate with financial calamity for all when a run on the banks caused a massive Depression in the fall of 1857. Before it was over, scores of financial institutions